1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose

Base Information

• Chemical Name: 1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose
• CAS No.: 76704-35-3
• Molecular Formula: C₁₅H₂₂O₈
• Molecular Weight: 330.335
• Mol file: 76704-35-3.mol

Synonyms:1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose

Chemical Property of 1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose

There total 17 articles about 1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

(1S,2S,3R,4R,6S)-4-(acetoxymethyl)-6-azidocyclohexane-1,2,3-triyl triacetate (97747-53-0) → 1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose (76704-35-3)

Guidance literature:

With 10 wt % palladium on activated carbon; hydrogen; In methanol; for 2h; under 1292.9 Torr; Inert atmosphere;

DOI:10.1002/ejoc.201100956

Reference yield:

acarbose (56180-94-0,68107-33-5,106864-09-9) → 1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose (76704-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Raney nickel / H₂O / 20 h / 25 °C / 750.06 Torr / pH 3

2: pyridine

With pyridine; hydrogen; nickel; In water;

DOI:10.1016/0008-6215(91)80045-O

Reference yield:

(S)-4-((4R,5S)-5-Ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-[1,3]dioxan-5-one (219622-91-0) → 1-deoxy-2,3,4,6-tetra-O-acetyl-5a-carba-D-glucopyranose (76704-35-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diethyl ether / 6 h / 0 - 20 °C / Inert atmosphere

2.1: potassium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere

3.1: acetic acid / tetrahydrofuran; water / 5 h / Heating

4.1: pyridine / 24 h

5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 6 h / 85 °C / Inert atmosphere

5.2: 10 h / Heating

6.1: ozone / methanol / -78 °C

6.2: -78 - 20 °C

7.1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / 0 - 20 °C

8.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

9.1: sodium azide / N,N-dimethyl-formamide / 48 h / 85 °C

10.1: 10 wt % palladium on activated carbon; hydrogen / methanol / 2 h / 1292.9 Torr / Inert atmosphere

With sodium azide; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 10 wt % palladium on activated carbon; hydrogen; tri-n-butyl-tin hydride; potassium hydride; ozone; acetic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; 2.1: Peterson olefination;

DOI:10.1002/ejoc.201100956

upstream raw materials:

acetic anhydride

1D-(1,3/2,4)-1-Hydroxymethyl-2,3,4-cyclohexantriol

acarbose

(1R,2S,3R,4R)-4-[(acetyloxy)methyl]-6-oxocyclohexane-1,2,3-triyl triacetate